Hydrochloric Acid → HCID 86721238, compound

HRID 1750392Notes

Reaction equation

HRID 1750392 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:12]=[N:13][N:14]([CH:23]([F:25])[F:24])[C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[S:9][CH:10]=1)C.[OH-].[Na+].Cl>C(O)C>[F:25][CH:23]([F:24])[N:14]1[C:15]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[C:11]([C:8]2[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:26])=[O:3])[N:7]=2)[CH:12]=[N:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86721239HCID 86721239, compound

Product 1

HCID 86721238HCID 86721238, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (0.380 g, 1.00 mmol) obtained in step 5 in ethanol (4.0 mL) was added 6N aqueous sodium hydroxide solution (0.500 mL, 2.99 mmol) at room temperature, and the mixture was heated under reflux for 30 min. After cooling to room temperature, concentrated hydrochloric acid was added until the mixture became pH 6. The reaction mixture was extracted with dichloromethane. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure to give (2-[1-(difluoromethyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl)acetic acid (0.320 g, 91%) as a yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. extractionThe reaction mixture was extracted with dichloromethane
  4. washThe organic layer was washed with saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b56b444f90f744df90ff1d7675a65468
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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